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Related Concept Videos

Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
Removing one hydrogen from the intervening CH2 group with both...
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Thermal and Photochemical Electrocyclic Reactions: Overview

Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
Radicals: Electronic Structure and Geometry01:07

Radicals: Electronic Structure and Geometry

This lesson delves into the geometry of a radical, which is influenced by the electronic structure of the molecule. The principle is similar to that of a lone pair, where the unpaired electron influences the geometry at the radical center.
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Electrophilic Addition to Alkynes: Halogenation02:38

Electrophilic Addition to Alkynes: Halogenation

Introduction
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.

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Related Experiment Video

Updated: May 31, 2026

Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates
06:35

Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates

Published on: February 15, 2016

Directed trilithiation enables entropically stabilized heavy-atom-centered triangulenes.

Hajime Gotoh1, Soichiro Nakatsuka2, Keisuke Kinoshita1

  • 1Department of Chemistry, School of Science and Technology, Kwansei Gakuin University, Sanda, Japan.

Nature Communications
|May 29, 2026
PubMed
Summary
This summary is machine-generated.

Scientists developed a new method to embed heavy main-group elements into triangulene frameworks, creating stable, bowl-shaped molecules with unique electronic properties. This breakthrough enables novel main-group architectures for advanced materials.

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Published on: July 28, 2018

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Last Updated: May 31, 2026

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Application of Elemental Lanthanides in the Selective C-F Activation of Trifluoromethylated Benzofulvenes Providing Access to Various Difluoroalkenes
10:10

Application of Elemental Lanthanides in the Selective C-F Activation of Trifluoromethylated Benzofulvenes Providing Access to Various Difluoroalkenes

Published on: July 28, 2018

Area of Science:

  • Materials Science
  • Organic Chemistry
  • Main-Group Chemistry

Background:

  • Embedding heavy elements into π-conjugated systems offers stability via geometric confinement.
  • Previous synthetic methods have struggled to achieve this incorporation effectively.

Purpose of the Study:

  • To develop a regioselective synthetic strategy for incorporating heavy main-group elements into triangulene frameworks.
  • To explore the structural, stability, and functional properties of these novel compounds.

Main Methods:

  • Directed, regioselective trilithiation of nitrogen-bridged macrocycles.
  • Synthesis of antimony-, bismuth-, tin-, and lead-centered triangulenes.
  • Single-crystal X-ray diffraction analysis.

Main Results:

  • Successfully synthesized heavy-atom centered triangulenes with deep bowl-shaped geometries.
  • Observed remarkable thermal and chemical stability despite strained structures.
  • Demonstrated reversible redox behavior in antimony-centered triangulene.

Conclusions:

  • A general synthetic platform for heavy-atom embedding in curved π-systems has been established.
  • Geometric confinement effectively enhances stability of these strained main-group architectures.
  • Topological embedding of heavy atoms leads to distinct functional properties, opening design opportunities.